Vacation rentals in Skipwith

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Top-rated vacation rentals in Skipwith

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Top guest favorite

The living area features a large window with sliding glass doors, allowing natural light to fill the space. A comfortable sofa and coffee table are positioned beside a dining area with chairs. A ceiling fan and subtle grey walls complement the wooden floor, enhancing the atmosphere.

Apartment in Clarksville

4.98 out of 5 average rating, 123 reviews

Cozy Getaway Efficiency on Buggs Island/Kerr Lake

Fully stocked efficiency on Bluestone Creek, Clarksville, VA. Will sleep 4 (queen bed and sofa sleeper). Best suited for a couple or will accommodate family up to 4. Covered deck overlooking lake. Quiet and secluded, surrounded by 28 acres of woods. Perfect for fishermen and recreation. Parking for boat/ trailer. Dock has electric. A canoe is provided. 15-minute boat ride to Clarksville. Launch is 4 miles from property. Private entrance, 2nd floor. No meals served. Over 10 yrs is an extra guest.

Guest favorite

A serene view of Kerr Lake is displayed, with sunlight glimmering on the gentle waves. Bare trees outline the shoreline, while a distant dock is visible against the clear sky, contributing to the tranquil lakeside scenery.

Home in Clarksville

4.9 out of 5 average rating, 156 reviews

TDF Retreat on Kerr Lake

Come enjoy your own space at your own pace, directly on Kerr Lake. Quaint two bdrm/1 bath house on the Lake. 90 minutes from Raleigh or Richmond. This charming home, sleeps five, and is just steps to the dock which you can tie your boat up to. Longwood State Park is the closest boat ramp, and a mere 10 minute boat ride from there. Spend nights watching the sun set and sitting around the firepit making smores. Nonsmoking property. No vehicles on the back lawn. Please review cancellation policy

Guest favorite

The exterior of a modern A-Frame cabin is framed by trees, featuring a striking triangular window that reflects warm light. A welcoming entrance is highlighted by a wooden door, while two outdoor chairs are positioned on a gravel patio, inviting relaxation.

Cottage in Warren County

4.85 out of 5 average rating, 150 reviews

A-FRAME Lake Cabin. Private Boat Dock, Kayaks, SUP

BRAND NEW (2022) custom lakefront A-Frame Cabin. Mid-Century Modern. You'll love the stylish cottage & all the outdoor living/playing. Close walk to your own private dock (2 boat slips) and boat ramps close by. Located right on Kerr Lake (aka Buggs Island). NEW for 2024; ALL NEW BATHROOM, NEW stable internet, concrete sidewalk, Solostove firepit patio, NEW hot tub, patio lights, gas grill, outdoor shower. Toys left out; wagon for hauling, kids kayak, adult kayak, paddle board, and beach chairs.

Top guest favorite

A small rustic cabin features a welcoming porch adorned with string lights. A picnic table and bright blue chair are positioned outside, surrounded by a grassy area and tall trees in the background. The cabin’s red roof contrasts with the white siding.

Farm stay in Hollister

4.98 out of 5 average rating, 184 reviews

Cozy Cabin & Farm stay @ Owl Tree Acres Homestead

Sunflower cabin is a sweet little rustic cabin with friendly homesteading artist/host located on Owl Tree Acres Farm. Cozy sleeping for 4, a dorm refrigerator, toaster oven, microwave, coffeemaker,. Wifi with desk and Smart HD TV are provided. A “separate” beautiful bath house is located near the Communal fire pit away from the cabin. No bathroom facilities in cabin. Pets allowed with $30 pet fee. No pit bulls, rottweillers or other agressive dog breeds allowed. No pets allowed on beds.

Top guest favorite

A charming sunlit cottage nestled on a green lawn, framed by trees. The structure features large windows, maximizing natural light. A patio with a gazebo is visible in the foreground, providing a relaxing outdoor space. The backdrop includes serene surroundings and hints of Kerr Lake.

Cottage in Clarksville

4.93 out of 5 average rating, 184 reviews

Lakefront Cottage w/ great view and use of dock

The sunlit cottage is perfect place to enjoy the largest lake in Virginia, exploring nearby state parks, the quaint town of Clarksville, or nearby breweries/wineries. The cottage offers an open view of the lake and use of a dock (150 yds from house) for fishing, swiming, docking watercraft or watching the sunset. A great retreat for a small family of 4 or 2 couples. Please indicate the number of guests; parties over 4 must be pre-approved. Reservation must be by an adult (age 21+).

Top guest favorite

A rustic log cabin is nestled among lush greenery, surrounded by trees. A grassy yard extends in front, with a vehicle parked nearby. The structure features multiple windows, showcasing its charming facade and creating a sense of tranquility in the natural setting.

Cabin in Keysville

4.98 out of 5 average rating, 140 reviews

Peaceful Log Cabin in the country.

Hand-Hewn Log Home on 1.5 acres with a newly added outdoor area in Sept 2025. 20 minutes to Pineview, Waverly and Pavilion @Mimosa wedding venues. 5 Minutes from town, 35/40 minutes to Longwood U and Hampden Sydney College. Zero traffic! Plenty of room - 2 bedrooms, fully stocked kitchen, Coffee & Tea Bars. Clean and cozy. The perfect place to unwind, unplug and reset your clock We strive to go beyond expectations designing our cabin the way Airbnb vacations once were.

Superhost

A calm lake scene is depicted, showcasing still waters that reflect the surrounding greenery. Dense trees line the shoreline, creating a serene backdrop. The overcast sky casts a gentle light over the landscape, enhancing the peaceful atmosphere.

Home in Warren County

4.93 out of 5 average rating, 114 reviews

Peaceful Lakefront Retreat

Enjoy the best Lake Kerr has to offer. Waterfront home with dock and sandy beach. In a quiet cove with deep water perfect for fishing or just sitting by the water watching the sunset- catch catfish right off the dock. Quiet family friendly community located in a peaceful setting. All the conveniences of home provided. Fire pit perfect for s'mores by the water. Lovely water view from the main living areas. Kayaks for use or bring your boat and keep at the private dock.

Top guest favorite

A red brick house is set amidst a grassy yard, featuring green shrubs and small trees. The structure has white window trim and black awnings over the windows. A covered porch is seen on one side, enhancing the outdoor space with shade.

Home in Clarksville

4.97 out of 5 average rating, 70 reviews

Country Living near Buggs Island/Kerr Lake

RUSTIC COUNTRY CHARM just minutes away from Buggs Island/Kerr Lake. This 2 bedroom, 1 bath home is perfect for the person/family looking to disconnect and relax for a few days. Surrounded by farmland, you are welcome to take a nature hike around the farm and soak up the beauty. Located 5 minutes from Staunton View Boat Landing and 15 minutes from the Town of Clarksville. During deer hunting season, arrangements can be made to use deer stand on the farm.

Guest favorite

A private dock is visible extending over the water, featuring two red Adirondack chairs positioned around a small table. Calm lake water can be seen, surrounded by trees and a distant shoreline. A clear sky with scattered clouds completes the serene scene.

Home in Clarksville

4.97 out of 5 average rating, 119 reviews

Perfect Getaway - Waterfront w/ Private Dock

Perfect getaway in this lakefront 2BR/2BA home! Private dock available for your use to enjoy year-round fishing and boating. Explore the quaint town of Clarksville, just 10 minutes away by water or road. Pet friendly. Canoe available for your use! This lakefront house is the perfect retreat for couples, small families, and fishermen! If you like to cook, please help yourself to our herb garden!

Guest favorite

The historic Bracey Train Depot features a charming white façade with a sloped metal roof. An inviting walkway leads to the front door, framed by a garden area. A large rock sits on a well-maintained lawn, surrounded by trees in the background.

Home in Bracey

4.94 out of 5 average rating, 131 reviews

Bracey Historic Train Depot

Want to step back in time to the late 1800's? Staying at the historic Bracey Train Depot will give you that experience and more. The Depot is among one of the surviving buildings with the old post office across the street, the general store next door and landmarks. This section of Bracey Drive is at times secluded, just around the 'cut' and a half mile from I-85.

Top guest favorite

The private log cabin features a charming facade with a sloped roof and a welcoming porch. The structure is surrounded by lush greenery and a well-maintained lawn, providing a peaceful outdoor setting. The pathway is lined with stones, leading up to the entrance.

Guesthouse in Halifax

4.97 out of 5 average rating, 241 reviews

Hunter's Retreat at Springfield 1842

Private log cabin with king size bed, kitchenette, bathroom on main level, two full size beds in the loft. Includes air conditioning and heating, sleeps up to 4 adults. Upstairs is accessed by a ships ladder so unfortunately its not suitable for all. 24 miles from VIR or around 30 mins drive time